Kickstart Your Portfolio Career: Part 5 of 5

How To Stop Corporate Cortisol Hijacking & Focus on High Value Work

Welcome to the final installment of a five-part miniseries, 'Kickstart Your Portfolio Career.' On August 27th, I am hosting a Free Workshop where I will dive deeper into each topic and what it actually takes to launch your portfolio career while maintaining your day job.

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In this week’s newsletter, I am writing about how working in a corporate environment can destroy our sense of what is urgent and important vs. just bullsh*t noise; and how we can get it back!

As a refresher, here is what we have covered so far:

Week 1 - How Habit Formation & Identity work play a pivotal role in launching my Portfolio Career

Week 2 - How I learned to make aligned decisions & discover what work lights me up

Week 3 - How I Built a Financially Stable Portfolio Career & Made My Side Hustle, My Main Hustle

Week 4 - How To Identify Upper Limits & Move Into My Zone of Genius By Leveraging My Human Design

The Day “War Rooms” Entered My Consciousness.

Picture a bright-eyed twenty-something woman in 2007, excited about a new consulting gig at a telecommunications company. She had been 'deployed' as a Project Manager, part of the team rolling out a multi-million dollar IT system.

Yes, that young woman was me. I arrived at my client's offices, ready to project manage the shit out of whatever assignment came my way. I was swiftly ushered into a room that resembled a boardroom, but the walls were plastered with endless pages of Gantt charts and highlighted ‘critical paths’. As I glanced around, I noticed three people in the corner, frantically printing out A0-size Gantt charts ahead of the 9:30 walkthrough.

Immediately, I felt a gut punch and thought, "WTF have I gotten myself into?"

This was the day the concept of a "War Room" entered my consciousness. For those of you lucky enough not to have endured one, a war room in a corporate context is a dedicated space where specialised teams focus intensely on solving complex problems, like deploying a multi-million dollar IT system.

I remember standing at the back of the room, listening to executives belting out demands to the Project Managers, saying things like: "THIS IS URGENT and needed to be done yesterday." The irony was palpable when no one could answer what the ‘most urgent’ task was for that day.

Perhaps you can sense from my tone that I didn’t last long there. Let's just say I may not have followed the 'critical path' because it seemed nonsensical, leading to an uncomfortable encounter with the lead PMO. Unkind words were exchanged, and that was that.

I'm sharing this experience because it was when I first noticed how distorted the concept of urgency vs. non-urgency is in most organisations. If an executive screamed loud enough to have that presentation on his desk by 9 a.m., we obliged. Did he read the presentation half the time? No, but that wasn’t the point.

Years of this conditioning left me frazzled, realising I never truly knew what was urgent for the business (other than deadlines for board or financial reporting). It all got swept up in the soup of 'everything is important', and so we acted accordingly.

Software Engineers Taught Me How To Deep Work.

Fast forward to 2018, and I'm living in London, starting a new role as a principal consultant for one of the world’s most reputable software engineering firms (they are considered to be part of the ‘ Founding Fathers of Agile’, IYKYK).

I could share countless incredible stories from this period (I loved this job, and the people were some of the best I’ve ever met), but today’s important lesson is how my software engineer colleagues re-taught me the difference between high-value and low-value tasks, how to schedule deep work, and why the most important meetings are held first thing in the morning to avoid decision fatigue.

Here are some examples:

• During our morning stand-ups, we assessed each new ‘ticket’ on the agile board (this might be a part of a feature that needed coding for the product we were developing). We would critically discuss whether that ticket was the most valuable next task for the overall product; if not, it was deprioritised & another ticket moved up in its place.

• In my first week, I scheduled team connect sessions between 11 a.m. and 1 p.m. All the software engineers declined without explanation—initially, I thought, ‘excuse me…’ After speaking with the Tech Lead, I discovered that the engineers never took meetings between 11 a.m. and 3 p.m. They reserved this time for deep work, blocking their calendars, turning off notifications, logging out of Slack, and focusing on writing code.

• Whenever the team needed to critically assess the backlog and make important decisions about which features to build next, a morning session was scheduled before 11 am. The team knew their decision-making ability diminished as the day wore on.

I couldn’t believe we were ‘allowed’ to own our time and make decisions as a team like this! I kept asking, ‘What if an executive demands this feature be built? Do we just do it?’ My question was met with blank stares. It was as if they had never encountered an egomaniac executive before.

Where To Play, How to Win & Aligned Execution.

When I first launched my portfolio career in 2019 while working full-time as an executive, my time was scarce.

I had approximately 2.5 hours each day (before work started) to make progress. I applied all my learnings about time management, task value assessment, and critical decision-making to the precious time I had.

It’s easy to feel overwhelmed when you're starting out because you're figuring out:

• How to align your skills with work that excites you (where to play)

• How to find the people who genuinely care about your work and will eventually find enough value you in it to pay for it (how to win)

• How to develop new skills needed to successfully launch successful income streams (aligned execution)

This is then overlaid with all the operational decisions, like:

• What email system should I use?

• Should I build a website?

• Do I start a Substack? (This platform wasn’t around when I first started)

• Which channels should I invest in to reach my audience? (I chose Instagram and LinkedIn)

As a solopreneur, it can be overwhelming to face the sheer number of tasks and decide what to work on at any given moment. This overwhelm is compounded when you draw inspiration from another creator or when a new trend emerges (e.g., TikTok). Maintaining laser focus is essential, yet the hardest to achieve.

Your mental game is critical at this stage—you must resist the temptation to jump into everyone else’s circus out of fear of missing out, while remaining open to pivoting and changing direction if things aren’t working or if a genuine opportunity arises.

How I Use the Eisenhower Matrix To Prioritise My Work.

Initially, when I started out, I was constantly context switching, which was a brain drain, and I felt like I wasn’t getting anywhere.

I went hunting for a framework to help me prioritise my tasks and think strategically about what I worked on and why. It was frustrating that I couldn’t get my act together because, in my day job, I ran multiple teams and launched new businesses.

But this was different. For starters, it was just me working on it, and it was mine (I was afraid of messing up). Secondly, I realised that the corporate world had conditioned my nervous system to run in multiple directions at once, with little focus on what needs to be done now versus later.

Years earlier, I had read the "Makers vs. Managers" essay by Paul Graham (published 2009), which helped me understand how to schedule tasks based on the nature of the work (and the importance of time blocking). But I needed a framework to help me categorise what was urgent versus not urgent.

This is when I started leveraging the Eisenhower Matrix. This is a time management tool, based on the urgency and importance of tasks; it helped me decide what tasks to do immediately, schedule for later, delegate, or eliminate. It consists of four quadrants:

1. Quadrant 1: Urgent and Important (Do First)

   Tasks in this quadrant require immediate attention and carry significant consequences if not completed. For example:

   • Growing my audience via my newsletter and consistently offering value, rather than constantly asking people to buy from me.

   • Solidifying my core income stream(s) and ensuring clarity in messaging of my offer.

   • Setting up an easy way for clients to pay me (e.g., using Stripe, PayPal, and integrating with a booking function like Calendly).

   • Serving clients exceptionally well and delivering value.

   Quadrant 2: Not Urgent but Important (Schedule)

   These tasks are crucial for long-term success but don’t require immediate action. This is essentially your Portfolio Career strategy—it’s important to make time to work ‘on your business’ as well as ‘in your business’. Examples include:

   • Developing a personal brand strategy and stepping into my ‘Rightful Authority’. This involved working on my mindset about showing up online and overcoming preconceived notions about what I to offer & that people would be interested in hearing them.

   • Engaging in skill building to enhance my skillset, aiding my portfolio career’s future direction (e.g., completing a Neuroscience in Business course at Sloan School of Management with Dr. Tara Swart).

   Quadrant 3: Urgent but Not Important (Delegate)

   Tasks here are usually interruptions that need quick handling but don't contribute to long-term goals. Examples include:

   • Ccreating and scheduling social media posts. I focused on delivering value instead of trying to keep up with all the algorithm changes and continuously modifying my strategy.

   • Sending out bespoke welcome emails. Where possible, I automate critical tasks like welcome emails and use systems like Zapier to ease my workload instead of doing every task manually.

   Quadrant 4: Not Urgent and Not Important (Eliminate)

   Tasks in this quadrant are distractions and don’t boost productivity. For example:

   • Spending excessive time trying to be active on all social media platforms. Initially, choose one or two and master them before expanding further.

   • Spending excessive time trying to create multiple new service offerings or income streams before validating and perfecting your core income stream.

Final Thoughts

I'd be lying if I said discovering these principles made everything fall into place—it didn’t.

Kickstarting my portfolio career was a blend of using frameworks and, importantly, having the right mindset. I was committed to embracing change and enjoying the journey rather than sprinting towards an unattainable perfect utopia—much like climbing the corporate ladder, which left me miserable.

Five years in, here’s what I’ve learned:

• Start before you're ready. It takes time for people to find and trust you. I began with my newsletter and focused on providing value before asking for anything in return.

• Expect evolution. What you start with might not be what you stick with. I began with startup coaching, but it didn’t fulfill me. Gradually, I transitioned to coaching solopreneurs on launching their portfolio careers.

• Patience with income. Don’t be hard on yourself if you’re not earning significantly in the first 6-12 months. While rapid success is possible for some, most of us need time to build sustainably. Focus on validing one income stream first & build from there.

• A portfolio career is a lifestyle. I think of a a Portfolio Career as an anti-hustle, pro-passion approach to work and life. It involves strategically considering your skills, the work that excites you, and taking control of your career direction rather than depending solely on one company for financial security.

Lots more on the final dot point to come.